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Search results; Over 1,000 homes in Islamorada

Guest favourite
Home in Islamorada
Boat slip included August-November 2026!
2 bedrooms, 3 beds, 2.5 private bathrooms
25 Jul – 1 Aug
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4.92 out of 5 average rating, 50 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
3–10 Aug
New place to stay
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Luxe
Villa in Islamorada
4 Bedroom Oceanfront Accessible Villa – Capacity 8
4 bedrooms, 5 beds, 4 bathrooms
2–7 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds, 3.5 bathrooms
2–9 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.96 out of 5 average rating, 147 reviews
Top guest favourite
Home in Duck Key
Private Pool Tropical Oasis - Centrally Located
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Oct
5.0 out of 5 average rating, 112 reviews
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 bathrooms
1–8 Aug
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed, 1 bathroom
22–27 Jul
4.91 out of 5 average rating, 34 reviews
Guest favourite
Home in Islamorada
Pristine Islamorada Pool Home with Ocean View and
2 bedrooms, 4 beds, 2.5 bathrooms
11–18 Aug
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
4.97 out of 5 average rating, 215 reviews
Guest favourite
Villa in Islamorada
Islamorada | Maison Residences
4 bedrooms, 5 beds, 6 bathrooms
22–29 Jul
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
9–15 Aug
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
24–31 Jul
4.96 out of 5 average rating, 25 reviews
Guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 46 reviews
Villa in Key Largo
Waterfront Luxe Pool, Hot Tub, Theater, Games&more
5 bedrooms, 9 beds, 5 bathrooms
16–21 Aug